Water → 2-Bromo-5-(cyclopentyloxy)pyridine

HRID 1966231Notes

Reaction equation

HRID 1966231 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][N:3]=1.[H-].[Na+].[CH:11]1(I)[CH2:15][CH2:14][CH2:13][CH2:12]1.O>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 73784IodocyclopentaneHCID 27628652-Bromo-5-hydroxypyridine

Product 1

HCID 578216902-Bromo-5-(cyclopentyloxy)pyridineYield 45%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

2-Bromo-5-hydroxypyridine (3 mmol) is dissolved in DMF (10 ml) and NaH (1.4 eq., 60% suspension in liquid paraffin) is added. After 30 min cyclopentyl iodide (2.2 eq.) is added and the reaction solution is stirred 3 days at 120° C. The reaction solution is pored into water and extracted with methyl-tert.-butyl ether. The combined organic layers are dried over MgSO4 and the solvent is removed in vacuo. 2-Bromo-5-cyclopentyloxy-pyridine is obtained after column chromatography (heptane/ethylacetate) as yellow oil in a yield of 45%; HPLC (method C): 2.08 min; LC-MS (method A): 2.05 min, 241.95 (M+H+).

Workup

  1. extractionextracted with methyl-tert.-butyl ether
  2. dry with materialThe combined organic layers are dried over MgSO4
  3. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-30c9f0dbc7ce44f280f526c9c14111a8
Source dataset
uspto-grants-2013_04
Patent number
US08420642B2

Reaction notes

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